


John's Kept Boy

by thewinchesterlifestyle



Category: Supernatural
Genre: Age Difference, Anal Fingering, Bottom Castiel, Butt Plugs, Cheating, DeanCas - Freeform, Keptboy Castiel, M/M, Name Calling, Orgasm Delay, Rough Sex, Top Dean Winchester, Top John Winchester, Voyeurism, johnstiel - Freeform
Language: English
Status: Completed
Published: 2015-11-19
Updated: 2015-11-19
Packaged: 2018-05-02 11:06:27
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,494
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5246021
Author URL: https://archiveofourown.org/users/thewinchesterlifestyle/pseuds/thewinchesterlifestyle
Summary: <blockquote class="userstuff">
              <p>He knew exactly what Mr. Winchester wanted, they had spoken about it in the beginning and Castiel enjoyed fucking. There was nothing quite like it and being Mr. Winchester’s kept boy saw him often bent over, pinned down or in a number of positions taking a nice, thick cock every single day.</p>
            </blockquote>





	John's Kept Boy

“You look perfect waiting for my dick. I love how you spend the day in nothing but lace and wait for me to fill that pert little ass of yours.” Castiel moaned when large hands massaged his ass, spreading his cheeks wide and causing him to clench down around the thick plug wedged inside him. “I should work from my home office more often. You’re such a good cockwarmer.”

Castiel spread his legs further apart where they were braced on the mattress. His hands were bound behind his back with Mr. Winchester’s tie and his cheek was smashed against the sheets. “Please fuck me. I need you...please Mr. Winchester!”

He knew exactly what Mr. Winchester wanted, they had spoken about it in the beginning and Castiel enjoyed fucking. There was nothing quite like it and being Mr. Winchester’s kept boy saw him often bent over, pinned down or in a number of positions taking a nice, thick cock every single day.

“I know you do. My pretty little slut has been neglected while I was working today.”

The plug was tugged out causing Castiel’s breath to catch in his throat and his ass to instinctively clench down at the missing toy. Mr. Winchester moved closer causing the mattress to groan at the shift. Lube was squirted directly inside his gaping hole and John was quick to shove his fat cock inside.

Castiel’s mouth fell open and he panted at the sudden intrusion. Behind him Mr. Winchester moaned his appreciation and used his knees to spread Castiel’s legs out further, pushing him into the position he wanted and immediately fucking forward.

It ached and burned as his ass adjusted to being full once again.

“Take it.” John grunted as the slap of his hips and balls against Castiel's ass rang out loudly in the still room. “Fuck. You’re my pretty little slut. You’re always so soft and pliant, waiting to take my dick at either end whenever I want.”

And Castiel was very well compensated. He’d take whatever Mr. Winchester wanted to give him.

“Ohhh! Oh fuck. Oh there. Please yes yes yes!” his eyes rolled and his cock ached, neglected and hanging between his legs, as John pounded into him from behind. His blood was singing, his body warm, as he shifted and jerked forward against the bed.

His moans and gasps of  _John oh oohhh John please please_  only encouraged the older man. The snaps of Mr. Winchester’s hips came hard and fast causing the headboard to knock against the wall, the mattress groaning under them.

“Moan my name. I want to hear it when I fuck you.”

“John John John please oh you feel so good please John. Harder harder John!” Castiel babbled and moaned, wanting a hand to touch him but John’s fingers only dug into him and yanked him back into each thrust.

Castiel didn’t notice the green eye watching from the cracked door, Mr. Winchester’s sons were supposed to be at practice or in class, as the pace picked up and he was right on the edge when a pleasured groan sounded.

Mr. Winchester’s hips jerked forward a few times and his softening cock slipped out once he caught his breath. “Fuck. I really wrecked that little hole of yours.” A thumb rubbed against his puffy rim even as Mr. Winchester’s come started to leak back out. “So gorgeous.”

He lay there in the middle of the bed, still completely naked, with his ass raised up and his hard cock neglected as Mr. Winchester admired his hole.

“I bought you a brand new set of pastels and picked up tickets to the gallery opening you mentioned.” Fingers lazily fucked his ass as Mr. Winchester spoke, “We’ll get you fitted for a suit for the opening tomorrow.” He could only nod and moan, shoving his ass back and wanting to trip over the edge. The other hand reached under and roughly jerked him off until he was crying out, going limp on the sheets.

The plug from before was pushed into his ass and his hands were freed as Mr. Winchester moved off the bed. “Thank you, sir.” He murmured for the gifts.

Castiel didn’t move from the large bed as Mr. Winchester cleaned up, dressed and mentioned a dinner meeting he was going to be late for.

He wasn’t sure how much time had passed before the door creaked open and Dean Winchester stood there framed in the doorway. “Dean.” He blinked and shifted up on the bed not even bothering to hide his naked state.

It wasn’t like he wore much around the house and both of Mr. Winchester’s boys had seen him either naked or wearing only sheer lace that hid nothing. Several times Castiel had noticed them when Mr. Winchester had been fucking him.

“Cas.” He could see Dean’s arousal, noted the flush to freckled cheeks and tried not to react.

Since he had become Mr. Winchester’s kept boy at seventeen he had steadily gotten more interested in Dean. It had started as a crush and had quickly developed into something close to love. He stared as Dean walked into the room, slowly stripping and moving towards him.

There was plenty of time to move when Dean, now naked, climbed onto the bed with him and leaned over him to kiss him softly on the lips. It was sweet and careful as a hand stroked against him. The contrast to Mr. Winchester’s rough, greedy touches and fucking, stole his breath.

“This ok?” Dean breathed against his lips and Castiel nodded silently, eyes hooded and cheeks flushed, while lips trailed down his neck and Dean’s erection brushed against his sensitive cock. “Fuck...you’re so beautiful.”

Feather-light touches had him relaxing against the sheets and his body slowly warmed with arousal once more. It was more than he could hope for and Castiel wasn’t going to question his good fortune.

Lips continued down, a tongue swirled around his nipple, until Dean reached his soft cock and carefully took it into his mouth. Castiel was still sensitive from his last orgasm and the sensation had him crying out, tiny hitching sounds more than audible to his own ears.

The whole time Dean’s hands stroked against him in soothing motions while his talented tongue and mouth continued to focus on his spent cock.

“Dean.” He breathed and fisted his hands in the sheets as he tried not to jerk up into Dean’s warm mouth. “Dean oh ohhh.”

“Shhhh I’ve got you, Cas.”

Castiel wasn’t sure what had brought this on but he could feel his eyes burning and tried to ignore how nice it was to have someone he loved touching him so carefully. He fell into the pleasure and the soft touches, gladly spread his legs when Dean had rolled on a condom and moved forward.

His plug was carefully removed, fingers stretched him and loosened his ass, before Dean was pushing forward. Castiel’s mouth fell open and his head shoved back as inch by inch Dean sunk into him. Dean’s cock wasn’t as thick as John’s but it still gave him a nice, full feeling that he relished.

As Dean rested inside of him soft lips pressed against his, lazily tasting and kissing, while Dean rocked his hips forward in an equally lazy motion. His fingers dug into Dean’s back and his heels dug into the backs of Dean’s thighs as Dean slowly fucked him.

“Beautiful.” Dean kissed his swollen lips, “Gorgeous.” Another kiss, “Perfect. Fucking Hell. You always look so perfect.” The words were followed by Dean’s lips against his neck, “You feel so good around me, Cas. You’re so good.”

Dean’s weight was comforting on top of him as they moved together slowly, carefully. “Dean Dean Dean please.” He didn’t know what he was asking for but Dean seemed to know. The soft kisses continued and when Dean pulled back it was to close a hand around his hard cock, slowly stroking him until Castiel’s mouth fell open and his cock jerked in Dean’s hand as he spilled his release.

“That’s it, Cas. You feel so good. Love how you moan my name.”

Castiel gripped at Dean as he continued to meet his thrusts. Dean’s orgasm came shortly after and Castiel fixed his eyes on Dean’s face, memorizing the way pleasure flushed his cheeks and had his mouth going slack.

When Dean pulled out he pressed a kiss to Castiel’s lips. He was careful when he pushed Castiel’s plug back inside and Castiel lay there, calming his racing heart, as Dean cleaned up in the bathroom and came back with a warm cloth.

He silently cleaned Castiel up, offered a soft smile and a parting kiss, before slipping out of the room and leaving Castiel sprawled out on the bed staring at the ceiling. Something in Castiel knew nothing would come of it but for now he'd savor the lingering feel of Dean inside him.


End file.
